Guest Post: Flattering Hats for Every Head

I’ve received several requests for some guidance about finding hats that work for specific face shapes. I’ve tried my hand at this topic before, but for real insight into the matter, I turned to my favorite milliner, Audi from Fashion for Nerds. How could someone who designs and hand-makes gorgeous hats steer us wrong, I ask you?

And, just as I expected, she’s outdone herself. So without further ado, I give you a comprehensive look at hat flattery by the incomparable Audi.

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From the 18th century until the mid 1960’s, hats were an essential part of any fashionable woman’s wardrobe. Milliners came out with new styles every season, and hats were purchased right alongside all the latest dresses, shoes, and jackets. As dress codes loosened in the ’60s and fashion began to cater more towards the young, hats gradually fell out of favor until the art of millinery was all but extinct. These days, hats still don’t enjoy the prominent place in our collective wardrobe that they once did, but they have begun to trickle back into fashion, and as they do, many women find themselves at a loss to figure out which styles suit them best.

TERMINOLOGY AND MEASUREMENTS
Now before I get into to choosing your best style, let’s talk about some of the basics of hats so that we’re speaking the same language. The two main parts of a hat are the crown and the brim, which are illustrated on the cloche style shown here.

Cloches are noted for their deep, rounded crowns, but there are numerous other crown styles out there: high and tall, shallow, domed, flat, creased (as in a cowboy hat or fedora), slanting and asymmetrical, flared, the list goes on and on.

Likewise for brims, the characteristics can very tremendously. Some are perfectly symmetrical and flat, some roll up, others angle down, some sweep up dramatically on one side and down on the other, and some hats don’t have brims at all. In determining which style of hat will suit you, you need to pay attention to the hat’s basic characteristics: the shape, height, and depth of the crown, and the width and shape of the brim. Below are a few examples of different hats and their basic characteristics.

Remember that there is a big difference between hat height and depth. One way to think about hat depth is to consider the distance between the top of the crown and the top of your head: if your head is “immersed” all the way in the hat, then the hat is deep; if your scalp barely breaks the surface of the brim, then the hat is shallow.

Below are two hats that are roughly equivalent in terms of the overall measurement from the top of the crown to the base of the brim; however, they are suited for very different faces. The hat on the left is deep and sits low on the forehead; the hat on the right is shallow and sits above the ears and high on the forehead.

By the way, many of these descriptors aren’t really standardized terms in the industry as far as I know, but I’m defining them here so that you’ll know what I’m talking about through the rest of the post. However, if you talk to any milliner and say you want a deep or shallow hat, for instance, I’m pretty sure they’ll know what you’re talking about.

HOW FACE SHAPE FIGURES IN
Now to apply some of these basic hat characteristics to your head. Choosing the right hat follows the same basic principles as choosing the right hemline, shoe style, sleeve length, or anything else: accentuate your best features and downplay the rest. A great place to start is to figure out what your basic characteristics are, so that you can determine which characteristics you’re looking for in a hat.

It’s helpful to know what the shape of your face is in order to get started; Imogen Lamport has a great tutorial here. Don’t get too hung up on trying to pinpoint exactly which shape you are; the important things here are the relationship between the length and width of your face, what the widest part of your face is, and whether your features are angular or rounded. Once you’ve examined these traits then the guidelines for choosing a hat should become fairly obvious:

Round faces: The idea is to elongate your face but also to balance it. Choose tall, shallow crowns to give it length, or try peaked, slanted, or creased crowns. Brims that are wider than your face help to help bring balance and make your face look narrower by comparison.

Square faces: Elongate your face by choosing a hat that sits high on your forehead. Soft berets worn all the way up at the hairline and tilted off to one side look great on you, as do rounded bowler hats with rolled narrow brims.

Long faces: Go with a flared, wider brim and deep crown to widen and shorten the face. Cloches are a good choice for you, especially if they have a wider brim.

Hearts and Diamonds: Since your chin is the narrowest point on your face, avoid wide brims that will make it look narrower. Otherwise pretty much any style will work well on you.

Angular features: If you’ve got angular facial features, such as a square jaw or triangular nose, then look for hats to soften and complement those lines; think sweeping or floppy brims, drapey berets, and sculpted, folded, or asymmetrical shapes. Also look for hats that have prominent, asymmetrical trimming, such as an elegant, curving arc of feathers.

Take a look at the photos below. Which characteristic of Paris Hilton’s hat works particularly well with her square jawline? Why is the shallow, wide-brimmed, peaked hat well suited for Ingrid Bergman? What makes the deep, wide-brimmed hat a good choice for Gwyneth Paltrow?

And how about oval faces? Well, there’s really no need to dwell too much on this one, because ovals can wear pretty much any damn thing they want. Don’t believe me? Well, using Imogen’s example of Kate Moss for an oval face, I pulled together this collage of her wearing some vastly different hat styles and shapes:

Yup, she looks great in all of them. So sue her.

OTHER FACTORS IN HAT CHOICE
Hats aren’t only about face shape though. You’ll also need to take into consideration your overall size, and for this you have a pretty simple guideline: the larger the woman, the larger the hat she can wear. If you’re plus-sized or tall, then a large, wide-brimmed hat will help to balance your proportions and won’t overwhelm you the way it would a petite gal.

And then there’s yet another characteristic that comes into play: your hair. The right haircut can allow you to wear hat styles that you otherwise might not be able to carry off; in this way, hats are a little more forgiving than other types of clothing. Long faces can be shortened with bangs (A.K.A. fringe), round faces can be slimmed with layers, and angular faces can be softened with waves and curls. If your haircut has done a lot of the work for you, then you can branch out a little and try some different hat styles.

And then, how you wear the hat is also a factor; when you’re trying on a hat for the first time, angle it this way and that, turn it sideways, tilt it far back or far forward and see which orientation works best on you, keeping in mind that as you style your hair differently, you may also need to style your hat differently. Remember, there is really no one “right” way to wear a hat.

Lastly, find a hat that fits you. This may seem like a no-brainer, but hear me out. Many hats have some amount of stretch to them, even the molded felt kind. A hat should generally fit snugly on the head but not be taut around the inner band, or else the shape will become distorted. If you’re buying a hat directly from a milliner, great; many milliners can adjust the size of their hats slightly or create a custom one just for you. If you’re searching for a vintage hat though, prepare to be patient and determined, because many vintage hats do not fit modern heads. What, you think that your head is unnaturally large because no vintage hats will fit you? Think again; vintage hats do not fit most people for several reasons: head sizes have increased (the average now is about 23” circumference), hats these days tend to be worn lower on the head where the circumference is larger, and then felt hats especially can shrink over time. An experienced milliner can reshape and even stretch a vintage hat, so before you just jam it on your head and destroy the shape, find someone you trust and make it fit correctly. Your head, and your hat, will thank you.

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One last note from Sally: Since many folks asked specifically about winter hats, bear in mind that this advice applies across the board. If you’re wondering if knit stocking caps look good on you, consider if a hat with a similar shape – like a cloche – would work.

….and also, I loved this post. I definitely have a hard time finding hats that don't look doofy on me! I either go for the bomber style, cloche or forget about it. One of the problems is that I have a supernaturally big head, so much so that finding glasses frames is difficult as well. Sigh…

So! Helpful! I have angular features, and you're SO right about the flattering power of softness and asymmetry. One question: I'm self-conscious about my profile, plagued with a largish nose and slightly receding chin. Do you have any advice for creating lines that strengthen (or, for my strong-chinned sisters, soften) the chin?

Great post. I have a few hats and was wondering if it possible to do something to a hat to make it a little smaller? I don't know if snaking some elastic inside would help or not. I have a plaid fabric fedora that I love the colors, but it's just too big.

What a terrific and useful post! I love hats and really need to wear them a) in winter re: freezing weather and b) in summer re: sun aversion. I have an EXTREMELY tiny head so most hats tend to overwhelm me – and to fall off. I've actually had them custom made (and bought vintage because old hats are smaller, like all vintage things).

I used to wear a cashmere beret that looked great with a former haircut. Looks stupid with my new one, which is too bad.

I am SO impressed that you make your own hats and you look gorgeous in all of them too. You really need hair peeking through from under a hat in order to look good in hats and I don’t have any of that with my super short pixie cut. But I love to admire hats on others!

I usually can't pick up a hat and buy it because they're almost always too small for me. But my head seems to be about 23", if I'm measuring it right. Do stores/vendors prefer to sell hats for smaller women? I would like to find something pretty to keep off the sun. The one hat I have is a little too small. I usually resort to baseball caps but I hate them.

Jamie: If you want to accentuate your chin, then look for deep hats where the brim frames out your face; this will throw shadows around the curve of your face and help your chin look more defined. Conversely, if you want to de-emphasize the chin, then avoid styles where the brim sits near the jawline.

Nadine: Why not try a mini hat or fascinator, which are designed to look small anyway and don't need to fit around your head?

Thank you, thank you, thank you, Audi, for sharing your toque tips with us. I love a well-made cloche myself and was very glad to see that you recommend the style for women with long faces, like me. (One of my favorite jokes? "Celine Dion walks into a bar, and the bartender says, 'Hey, why the long face?' ")

For everyone who posted about having a hard-to-fit head — I feel for you! I have not only a big head but also a lot of hair. If it weren't for the wonderful woman who started a hat store in my city and carries a range of sizes, I'd never find one to fit. Milliners rock.

I really REALLY want to branch out and try hats – my head is so small, though! I always have a hard time finding one that fits me! But I love the top hat and the 40s-style one that you featured – i really want to try!

Lady Cardigan: If you have felt or straw hats that are a little small, you can try getting them stretched at a dry cleaners or with a professional milliner. I have also noticed that stores do tend to carry limited sizes, and many are on the small side for some reason. This is probably why so many people think they can't wear hats! Keep trying; your head size is about the average, so a good shop should be able to fit you no problem.

Your post was very informative, thanks!!! I have an awful time finding hats that look good on me. My face shape is oval or elongated but not as angular as Kate Moss (my cheek bones are only slightly wider than my jaw)… I guess more like Liv Tyler. My hair cut is pixie style with short, side swept bangs. I find that most hats I try just totally hide my hair and I don't feel this is a good look for me. I might have to try one that sits on top of my head a little more? Do you have any suggestions? Thanks!

You and Audi are godsends! <3 I love wearing hats-they're wonderful accessories, but I always get the comment 'I wish I could pull off a hat like you do'. While I'm more than happy to shop with and offer advice to my hat-fearing friends, I've never really been able to articulate what makes a particular hat right for them. Now I have something to pass along to answer that question =)

Audi – great post. I follow you on Fashion for Nerds too. Almost any kind of hat used to look good on me — for whatever reason, I had a good "hat face." But now I'm over 50 (alas,) and my lovely vintage & novel hats that used to garner such compliments now make me look downright silly. What's a hatchet-faced old broad to do?

This was a great post, and very informative. I have always liked the look of hats, but find they never look very good on me. Hopefully I can find something that does now. I have one question, though. I have very short hair, sort of a pixie-cut. I've noticed that hats tend to look better with long hair that flows out underneath it. Any advice for making hats work with short hair?

Can you provide guidance on berets, both structured and the winter floppy style (often seen with a chunky-gauge knit)? I have a cloche-friendly face and after reading your post I figure there has to be a way. It must depend on how much I can deepen the crown without looking silly.

For the structured flat ones designed to deepen ~1 inch, I don't look good until ~2-3 inches. Looks weird to my eye but maybe it's not. The floppy ones look better when worn deeply, but the deeper dome tends to fall too far back, making me look like I am hiding dreadlocks. Should it go across the forehead and not hairline?

I love this — definitely going in my bookmarks list. You have inspired me to keep looking for the perfect hat and the perfect way to wear it. My noggin is getting pretty cold lately so I hope I'll figure it out soon!

Any tips on how to match hats to your outfit, not only the face shape? 🙂

I am so happy to see someone talking about hats. I do NOT love hats because I literally have to wear a wide-brimmed hat (at least 4 inches) every single day because of severe problems with the sun. (Yes, this is on top of 60 SPF sunblock.) The only days I don’t wear a hat are days when I’m using an umbrella or staying in my house.

It’s not so bad in summer, but wide-brimmed winter hats are hard to come by. Mostly they are dressy hats but I need it for walking to work in sub-zero weather, snow, wind, etc.

Is there such a thing as a stylish (or at least not hideous) wide-brimmed winter hat?

After becoming electrosensitive, I had to start wearing hats lined with a fabrics that helps shield from wifi (microwave radiation). Not a complete fix by any means, but helps some & always on the lookout for cute hats to line. Thanks for the post!

Hi Audi, I am an eastcoast milliner and took a class with Wayne Wichern too. I must say that I also like to mention that shoulder line and width whether square or drooped can make a big difference on how a hat looks. Bigger squarer shoulders can handle wider brims. Drooped shoulders need softer angles or up turned brims. For example Diane Keeton looks good in the derby hat because she has drooped shoulder line. But thre one thing that I think trumps everything else is the color of the hat. Wear hats in the colors that are either in your hair, skin or eyes. They will be a person’s best.

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Thanks for this excellent article. So many people admire my hats and then tell me they don’t own a hat because they ‘can’t pull it off.’ I firmly believe they have not tried on a hat to fit their face shape. After all, how did everyone’s great grandmother look smashing in hats?

1. Great article! Love it, I always thought my head was big because all hats are snug/tight on me. I just measured and my head’s only 22.5″. I LOVE hats and have a few but I have the problem of them leaving a line straight across my forehead. I still love them and buy them here and there but they only languish in my closet.:sigh: I would love the hat that Jolie is wearing.:) I have a diamond shaped face, my face measurements are only an inch apart.

2. What is up with that golf talk?

About Sally

Sally McGraw is a Minneapolis-based freelance writer, blogger, and editor.